


Private Dancer

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF
Genre: Alternate Universe, Alternate Universe - Crack, Blow Jobs, Conan O’Brien - Freeform, Crack Treated Seriously, Cunnilingus, Exotic Dancer!Conan, Explicit Language, Explicit Sexual Content, F/M, One Shot, Oral Sex, Sex Work, Sex Worker!Conan, Stripper!Conan, Strippers & Strip Clubs
Language: English
Status: Completed
Published: 2020-07-30
Updated: 2020-07-30
Packaged: 2021-03-06 04:35:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,940
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25617454
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan O’Brien has been working as an exotic dancer for two years and has become somewhat jaded when he encounters an enticing woman at a bachelorette party.
Relationships: Conan O’Brien/Original Female Character
Kudos: 4





	Private Dancer

**Author's Note:**

> If you enjoyed this, please leave a comment or feel free to come say hi on tumblr at fandomtransmandom :-)

Pressing down on a particularly wrinkled corner, Conan smearing the last few digits of a faded phone number on the twenty dollar bill. _A twenty? The audacity_. He thought as he continued ironing. Women would often jot their numbers down on a $50, or even a $100 before slipping it into his g-string, but he never dialed a single one. And a twenty certainly didn’t stand a chance.  
Setting it aside, he picked up a crumpled ten and laid down the iron. After his first week dancing he’d made the mistake of going to the bank with a large paper bag full of sweaty, crinkled bills. The middle-aged teller stared at him disgusted as she unraveled each one, looking as though she wished she were wearing a HazMat suit. Ever since, he spent the better part of his Monday afternoons off ironing money.   
Passing over another Lincoln, he thought back to the first time he wanted to dance on a stage. _Tap dancing lessons_. He certainly hadn’t seen himself performing like this. When he first started at the club it had been thrilling. The screaming pulse of the crowd of women, and of course a couple tables of men, got him rock hard as he undulated before them, casting clothes aside as money rained over his pale flesh.  
But now, two years later, Conan found himself having to pop a blue pill at least one night a week, passing on going out with the guys after the performance was over, and holing up in his apartment during his off hours, reading alone and ignoring any texts he might get.  
Looking at the time, Conan sighed. He had a bachelorette party in two hours and he had to start getting ready soon. Jumping in the shower, he let the water plaster his orange hair against his skin, rivulets of water trickling over his torso as he leaned his head against the wall. Emerging, he scrubbed his beard with the towel, peering at himself in the mirror. Sometimes he wanted to shave it, but he found last time that impeded his tips, so fluffing it a bit, he resigned himself to keeping the dark orange facial hair around.  
Conan pulled on his black leather g-string and breakaway pants, topping it off with a tight athletic shirt in deep purple. He knew some people thought he was too skinny, but once he got the g-string off there were never any complaints.  
Rifling through his bag, Conan searched the apartment for his Bluetooth speaker, finally finding it tucked behind his acoustic guitar in the living room. Tossing it in, along with a fresh can of whipped cream from the fridge, he took one last glance in the mirror to check his hair and teeth before scooping up his bag and climbing in his ancient Taurus.  
Turning off the engine in front of the house, Conan sighed heavily. _Fucking bachelorette parties_. He preferred to do them with one of the other men from the club. Robbie, or even Hal. When it was just him in a room full of drunk women, they could become positively rabid, and he’d never been adept at reeling them in.  
He clenched his hands and let out a deep breath, taking the bag from the car and approaching the door. Knocking, he could hear a jumble of women’s voices wafting to him before it opened to reveal a short brunette, swaying a little on the spot in her inebriation.  
“Woo! The entertainment has arrived, ladies!” She called out and a roomful of voices _woo’ed_ in response like some kind of bizarre mating call.   
Conan flashed his wide smile, following her into the house and taking a moment to set up his music before turning to the group.  
“Now who’s the lucky lady?” Conan asked, lowering his voice, and the women all pointed at a blushing blonde in the middle of the couch, even though it was painfully obvious by the ‘Bride-to-Be’ sash across her torso and the plastic veil on her head. “Well then,” Conan pressed play on his phone, and the sound of Tyla Yaweh’s _Salute_ filled the air. “Let me show you what you’ll be missing.”   
Conan always started out gently. A lot of the guys at the club swore by ‘go hard, go fast,’ saying that’s what got the best tips, but Conan worked differently. Trailing the backs of his fingers down the side of her face, he delicately slid across her neck to weave his hand into her hair, doing his best to maintain eye contact as she giggled and covered her mouth.   
Hips rotating with aching slowness, Conan leaned in, face close to hers, crystalline blue eyes moving up and down gradually as he grazed her cheek with his beard. The women shrieked and clapped around him as Conan placed one knee alongside her on the couch, reaching down to pull up the hem of his shirt and expose his abs. A bold woman next to the bachelorette reached up to touch him, fingers running through his sparse orange body hair, and her friends squealed.   
Removing his shirt the rest of the way, Conan sank to his knees, cupping the bachelorette’s hands in his own and bringing them near his firm chest without laying them down. She pressed forward timidly, rubbing him a little, before snapping her hands back as though she’d burnt herself on the stove.  
Grinning salaciously, Conan stood and swirled his hips, reaching down to undo the zipper of his pants, which provoked a high-pitched cry from the room. Though as Conan reached down to grab the fabric at his thighs, he turned and noticed a woman with dark auburn hair sitting in a chair, legs crossed and sipping champagne. Unlike the boisterous bunch around her, she neither screeched nor clapped, but sat silently studying him, lips pursed and eyes narrowed while the cacophony carried on.  
Curious, but determined to remain focused, Conan tore away his pants and the ladies screamed as he spun them once overhead before tossing them aside. Just then _Closer_ by Nine Inch Nails came on the playlist, a guaranteed tune for making a group feral. Expanding his radius, Conan worked the room, eager hands exploring his flesh as he ground before them, flirting and tickling, smiling and winking. One thing he would always love about this job is that look someone got in their eye when he made them feel beautiful.  
Half hard, Conan focused himself internally until he felt his erection raging against the leather of the g-string, and waiting for the climax of the song he snapped it off, the feminine raucous deafening as he dropped to his back, pressing his feet into the floor and thrusting into the air while he grazed his thick cock with his fingers.   
Standing and making a circuit of the room, some of the women bravely reached out to tug his cock, others too bashful, and when he collected the whipped cream from his bag the same ones who touched him were the ones who licked the sticky sweet foam from his chest, his abs, and in some cases even the tip of his cock.  
All the while the auburn-haired woman stared quietly. When _Lovesick_ by Trevor Daniel radiated over the speaker he was passing by her, and a hand snapped out to grab his. Eyes meeting, expression serious, she set down her flute of champagne, grabbing him by the hips and sinking to her knees, wrapping her lips around his cock without warning, all the while her luminous green eyes never parting from his own.   
Friends cheering, she hollowed her cheeks, taking him deep and working his shaft with one hand while the other reached behind his balls and applied steady pressure in small circles. Gasping, Conan inadvertently closed his eyes and let a hand rest on her head. He was used to women blowing him at these parties. Well, _trying_ to blow him. Usually it consisted of someone laughing with his cock in their mouth, sloppy lips and fingers barely able to coordinate, and it never even remotely felt good. But _this_ …  
Tensing, Conan knew he had to stop her or he was going to cum in her mouth in the middle of a room full of cheering women.   
He reached down and delicately pushed back her shoulder, shaking his head slightly. Sitting back on her heels, she raised one eyebrow and the ghost of a grin appeared on her face before she resumed her immobile position in the chair.   
The rest of the party proceeded as per usual, and Conan went through the awkward process of dressing and collecting payment at the end before gathering his things and heading home. Once again under the rush of the shower head, Conan found himself thinking back to those red lips poised around his cock, and began to grow hard. He wasn’t one to masturbate too often, living in such an oversexed environment all day it didn’t appeal much, but as he took himself in hand, imagining burying himself in her tight, warm throat, he came hard and fast, cum trickling over his freckled fingers and washing away as he envisioned those emerald eyes staring back into his own.  
**

It was Friday night and Conan found himself waiting backstage in his leather chaps and vest. Peering out over the crowd, he saw the usual mix. Tables of various women, a couple of bachelorette parties, a few tables of guys. Some of the dancers got squeamish around the fellas, but Conan always enjoyed them. They tended to be exceptionally polite and large tippers. There was apparently something about his body type they found appealing.  
“Alright you lovely ladies (and of course the gents) are you ready for _Conaaaan the Barbariannnn_?!” The announcer called over the speaker. Resounding cheers and claps greeted him and he slid on his knees to the stage as _Or Nah_ by Ty Dolla $ign started to play. Conan loved dancing to this song, it was achingly erotic, and as he undressed with tantalizing slowness, grabbing the pole with his strong arms and throwing himself upside down, only to spin gracefully to the floor, he closed his eyes and let the crowd fall away, losing himself in the music. Finally naked and erect, he lay against the stage, doing a modified push up as he ground his hips into the floor suggestively, bills fluttering around him. Making a circuit of the room, _I Mean It_ by G-Eazy began to pulse through his skin as aroused fingers slipped bills into his thigh belt, Conan brushing his hands over smiling faces and flushed skin.   
When the song came to an end, he gathered up his costume and his tips from the stage, changing back into his t-shirt and jeans before making his way out to the car.  
“Hello,” a throaty voice uttered behind him. Turning around, he saw her. The redhead from the bachelorette party, leaning against the wall of the club in a tight black dress that left little to the imagination, exhaling a large plume of smoke.  
“Uh…hi,” he swallowed. She’d caught him off guard, and watching her wrap her blood red lips around the filter of that cigarette was making him itch.  
She tilted her head towards the door. “Good job in there.”  
Conan nodded. “Thanks.”  
Dropping her cigarette and grinding it out with the toe of a black stiletto, her eyes pierced his again. “So is your name really Conan?”  
“Yeah,” Conan shifted his bag to the other side, pausing. “What’s your name?”  
“Evelyn,” she continued to stare. “But everyone calls me Eve.”  
_Fitting_. Conan thought. _Sinful_.  
“So,” Evelyn held up her hand, inspecting her fingernails. “Do you do…extras?” Those eyes flicked back to his, their intensity almost overwhelming.   
Conan clenched his sharp jaw. “Yeah, sure…sometimes.”   
Evelyn nodded thoughtfully. “How much?”  
He wanted to tell her not to worry about it. Wanted to tell her he’d take her home and fuck her all night for free. But then he remembered that stack of overdue bills crowding his kitchen table…  
“Five hundred,” Conan stated, biting the inside of his lip, afraid he might’ve gone too high. It wasn’t his first time, but it had been a while, and before he’d been desperate and settled for a lot less.  
Evelyn raised an eyebrow. “Done. Let’s go.” She began walking toward a black BMW and pressed a key to unlock it. “You can follow me to my house.”  
Nodding, Conan crawled self-consciously into his run down Taurus, heart hammering in his chest as he managed to keep up with Evelyn. Pulling into a ritzy neighborhood, she drove up a spacious driveway before a massive house, swinging her shapely legs out of the car and locking it with a beep.   
Standing behind her, Conan waited while she opened the door and disarmed the security system, stepping into the airy foyer. Peering around, his mouth gaped. He’d never been in a home this big, and as he looked at the art adorning the walls, the high end appliances, the expensive furniture, he was desperately curious what she did for a living, but figured it wasn’t his place to ask.  
Walking into the living room for a moment, Evelyn reappeared with her pocketbook in hand, withdrawing five crisp hundreds. Conan took them sheepishly and shoved them in his back pocket.  
“Come on,” Evelyn stepped out of her shoes and gestured for him to follow her upstairs. Flipping on the light, Conan saw her bedroom had large French doors with gauzy curtains and a plush-looking bed adorned with far too many pillows. Evelyn turned to him, reaching down to pull his shirt over his head before lovingly caressing his freckled torso. Conan encircled her waist, leaning in to fuse their mouths together, tongues dancing as he reached back to unzip her dress. Fabric fluttering to the floor, he revealed a black lace bra and panties, and he cupped one strong hand over her breast while her hand crept down to unzip his jeans.   
Undoing her bra and tossing it aside, Conan massaged her breasts while tilting his head to deepen their kiss, his hand exploring downward to make its way between her thighs, when Evelyn suddenly stopped him, shaking her head. Instead she hurriedly pulled his down along with his boxers, dropping to her knees and taking Conan into her mouth, tongue wrapping around the head of his cock as she thirstily swallowed his substantial length, moaning around his flesh.  
“Oh _fuck_ ,” Conan groaned, hips rocking into her throat as she took him deeper, hand twisting and jerking in time with her movements and cradling his balls gently.  
“Stop, _Stop_ ,” he panted. “Or you’re going to make me cum,” she pulled off, wiping her mouth. “And I want to fuck you still.”  
Evelyn stood, nodding, hooking her thumbs under the waistband of her panties and discarding them. Conan got rid of his pants, joining her on the bed. Climbing on top of her, he rubbed his turgid cock against the slickness of her slit before teasing her with the tips of his fingers, coaxing small mewls from her throat.  
Kissing and nibbling his way down her body, Conan positioned himself between her thighs, separating her lips with two fingers before he circled her clit with his tongue, tightening his movements until he applied direct pressure. Evelyn rotated her hips against his strong jaw, breathing hard and directing his head with her hands. Inserting two long fingers deep inside and curling upwards, Conan began to pulse against the soft tissue, sucking hard on her clit at the same time, causing Evelyn to cry out and thrash, her fingers pulling on his orange hair as she convulsed violently above him, body finally collapsing.  
Kissing his way back up her body, the look of her lust-laden eyes made Conan’s heavy cock twitch as he positioned at her entrance.  
“Ready?” He asked. Evelyn nodded weakly. Tipping forward, Evelyn’s back arched as Conan sheathed himself inside. Swirling his hips, they developed a rhythm, Conan fingering her clit as she rutted against him to meet his every stroke.  
“ _Harder_ ,” Evelyn begged, clutching his shoulders. Angling his hips upward, he began to pound into her with a frenzy, and Conan saw her eyes twitch and felt her flutter and clench around him as she came again, gasping his name. The constriction around his cock was exquisite, and Conan tucked his face against her neck, breathing hot and wet, hammering into her with abandon as his orgasm threatened to overwhelm him.  
“ _Fuck, Eve, fuck, FUCK_!” Conan let out a high keening moan, hips jutting forward irregularly one last time, Evelyn cumming with him, before his body deflated. Panting, he lay against her for a moment before rolling off, both spread wide on the bed as they waited for their sweat to dry.  
“Worth every penny,” Evelyn patted his shoulder once she caught her breath.  
Conan turned to her, smiling. “Satisfaction guaranteed.”   
Standing to get dressed, Conan looked around the luxurious bedroom, unable to fathom what this kind of lifestyle might be like.  
“Hey,” Evelyn lay, still naked, on the bed. “Would you be opposed if I called when I need your…services again?”  
Conan smiled. “Not at all.” Giving her his number, she walked him downstairs. Evelyn pulled him in for a surprisingly tender kiss at the doorway, and Conan found a part of him wanted to stay, wanted to wake up next to her in the morning. But they said their goodbyes, and as he backed his Taurus down the long driveway, Conan found himself grinning.


End file.
